


Girls Day Out 2

by khorybannefin



Category: Supernatural
Genre: Crossdressing, F/M, Fluff, Gen, Humor
Language: English
Status: Completed
Published: 2018-07-02
Updated: 2018-07-02
Packaged: 2019-06-01 06:39:51
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,671
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15137318
Author URL: https://archiveofourown.org/users/khorybannefin/pseuds/khorybannefin
Summary: The boots have to go undercover in the most uncomfortable way possible.





	Girls Day Out 2

Girls Day Out 2

Author: khorybannefin

Author Gender: Female

Reader Gender: Female

Word Count: 3670

Summary: The boys have to go undercover to solve a case, but in the most uncomfortable way possible.

Warnings: Fluff. Mentions of violence. Secondary embarassment.

 

"Uh-oh."

Sam was staring intently at his laptop screen and had that concerned little wrinkle in his forehead. You stopped digging through your bag and Dean looked up from the bed where he'd taken his guns apart. You turned to the younger Winchester with a hand on your hip.

"Uh-oh what?"

"Well, we came down here because the victims were getting their hearts cut out, right?"

"Yeah? And?" 

You made a motion with your hand, wordlessly trying to get him to spit out the bad part of the case. Not that the case wasn't bad enough. There were three bodies so far, and it hadn't been a week since it started. Whatever was responsible hadn't been in town long. At least that was your guess. Would be just like life to throw a horrible curveball. That's just the kind of luck you guys had.

"There was a detail they ddn't release to the press..."

"Just spill it, Sammy." Dean said, impatience in his voice as he rolled his eyes. Sometimes the big nerd was so damned dramatic.

"The vics weren't regular street walkers." Sam cut a glance at Dean. "They were transvestites. All of them." You raised your brows at Sam.

"What, really?" It definitely seemed like an odd target, and very specific. "All guys, huh. Hmm..."

"Ah for the love of crap." Dean tossed down the rag in his hands. "How the hell are we supposed to track something like that? Who ever heard of a monster only hunting guys in drag?"

Sam was looking at you. He had an expression that said he'd probably followed your train of thought and wasn't liking it at all. You started grinning, and it wasn't a nice expression. You looked at Sam at Dean's question about tracking and the grin just got wider. He started shaking his head, putting his hand out like he could stop you from speaking.

"Oh no, Y/N," he begged. "Please no!" Dean looked back and forth between you, clearly confused.

"No, what? What am I missing?"

"Y/N has a plan," Sam put his head down, pinching the bridge of his nose and squeezing his eyes shut. Dean looked to you, still puzzled. The grin got more evil.

"You're going undercover!" You crowed. It took a second to filter into Dean's brain. Sam just groaned, but Dean recoiled in horror.

"Oh hell no!" He stood up and shook a finger at you. "That's not happening. You put that out of your head right now." You stuck both hands on your hips.

"You know," you jutted out your chin defiantly. "I was just going to dress up Sam, but now I think you should both go. Double our chances."

"I'm not kidding. You aren't getting me in a dress. I don't care what the circumstances are." Dean stopped his angry pacing and turned to you.

"Wait, why just Sammy?"

"Because he's prettier."

Sam laughed, his whole face lighting up and dimples flashing. Dean started choking on anger. He pointed a belligerent finger at his brother, his look warning.

"You shut up." He stormed up to you, forcing you to look up at him. "What do you mean he's prettier? I ain't had any complaints, in case you hadn't noticed. I'm a hot ticket item."

"Yes Dean," you said, rolling your eyes. "You are very hot as a man. You're even already a whore, which helps. But it'll take a lot more effort to put you in drag and make it remotely believable."

"I am not a whore," he hissed. Then stood up straight, holding his head high. "I bet you I can make a prettier girl than Sammy." You jumped all over that, shaking his hand before he could think about it and grinning like a loon.

"I'll take that bet!" Sam groaned again, dropping his head and banging it against the cheap table a few times. Sam already knew. He didn't have long to wait before Dean realized what he'd done, popping his mouth off.

"Son of a bitch!"

"No take backs, Dean!"

You strutted over to your bag, digging into it and looking at clothes, just thinking, planning. Dean raged around the room, pissed that he hadn't seen it coming and blaming Sam for letting him run away at the mouth. Sam protested, hands up defensively. It was never Sam's fault. Dean could get in his own trouble. Besides, Sam knew he was doomed from the first. They'd never been able to get out of your crazy plans. The sad part was, crazy as they were, they had a tendency to work.

"I have good news and bad news." You turned back around, a shirt in your hands that was clearly only going to fit you. Dean winced.

"How much worse is it going to get?"

"Well," you drew out the word, building suspense. "No spa this time."

"Oh, thank god." Sam breathed. It had taken weeks for that waxing to stop itching as everything grew back. No man should ever have to have whisker burn in their pants. He couldn't help but be grateful.

"But!" You pointed upwards with a finger, halting their trains of thought. "There will have to be beauty school, hair, and wardrobe shopping."

Sam ran his fingers self consciously through his hair. Dean always teased him about how long it was, but he didn't want it cut. In fact, he didn't want anything done to it at all. Dean just stared, blinking, thoughts racing through his head. He was obviously imagining himself with lipstick and a dress. He looked vaguely green around the gills.

"I'm not shaving my legs," he said with finality. You just cracked up. You couldn't help it. You had been trying to hold it back for the last ten minutes.

"Fine," you said, giggling and trying to get your breath back. "No leg shaving. Knee high heeled boots for you." 

You winked at him and he glared, jaw tight. He'd really thought that was going to end the whole debacle. He should know better by now. In fact, so should Sam. You realized he had no clue as your eyes moved over to him. His eyebrows went up and he started shaking his head. You cut him off.

"Come on Sam. You can't both be in boots." You stalked up to him, smiling, and gripped his leg just above the knee. "Besides, you have such sexy legs."

"Stop!" He sighed, brushing your hand away. "Just stop. Fine. I'll shave. Please tell me I don't have to wear stockings too."

You assured him that he wouldn't. You also told him that you guys could probably either do waxing on his legs or Nair or something. You remembered too well his complaining about the hair growth last time. And honestly you didn't want to watch him butcher himself with an actual razor. Guys were absolutely useless at shaving anything but their faces. Sometimes not even that.

You stole Sam's laptop and started looking things up. There was only going to be a few places where you could get clothes and shoes that would fit the boys. Especially Sam. That boy was built like a mountain, and none of it soft. You were wondering if you could talk him into something with a corset top. It would be a hell of a lot easier to create the illusion of breasts if you could narrow his waist a little and fluff the pectorals he was sporting. You kept giggling as you typed and scrolled and both boys looked ill. They skipped past the evening beers and went straight for whiskey. If they were looking for courage they were not going to have much luck in a bottle.

You managed to pick up a couple of good leads on wardrobe. Hair and makeup would be harder. You could curl Sam's hair, you supposed, but there was no way Dean's natural hair would work. Even glitter gel wasn't going to make up for how short it was. A wig was the only answer. That, funny enough, was easier to find than anything else you were looking for. This was going to require a lot of work tomorrow. You had to move quick. You never knew when your target would attack again. And it was hit or miss that either of the boys would attract the killer. But it was the best plan you could think of.

"All right, ladies," you said, standing and stretching. "Get your beauty sleep. We have a long day ahead of us tomorrow."

"You're evil, Y/N," Dean groused. "It's your worst feature."

"I know love," you pecked him on the cheek before throwing yourself into the bed. " But you love me anyway."

********

You woke the boys up at an ungodly hour, as Dean did not hesitate to tell you, repeatedly, as you ushered them out of the motel and into the car. Sam was blinky. He clearly needed coffee. Dean, on the other hand, was just a bear. He still had pillow marks on his face! It was adorable. You gave in and let them stop somewhere for breakfast. Wouldn't do to have them both complaining all day. Well, any more than they already would just because of the situation.

"So," Sam said, head down in his third cup of coffee. "What's the plan?"

"First up is going to have to be clothes and shoes. It's going to take the longest. Especially with you, big boy." You poked him in his overly muscled chest. "Even regular drag shops don't really make anything in Sasquatch size."

"Hey," Dean piped up in his brothers defense, or so you thought. "Don't sass the squatch." He started laughing. Sam sighed and threw a piece of toast across the table.

"Thanks a lot, Dean. I love you too." He leaned across into his brothers face. "I'm going to love seeing those bow legs of yours try to walk in heels. You're going to look like John Wayne in a dress." Dean inhaled, his face setting, and started gesturing at Sam with a slice of bacon. You cut them off.

"All right, you two little brats can just cut that shit out right now." You waved your hands between them, breaking their eye contact as they glared daggers at each other.

"Yeah, Dean," Sam sneered. "Cut it out, brat."

"I'll give you brat!"

You leaned over, slapped a hand over each boys face and shoved them back in their seats. You really weren't expecting them to degenerate into this much bitchiness so soon. You might think they were getting into character, but you knew better. They were brothers and they were secretly little boys inside. Times like this their inner child wasn't so hidden.

"Knock it off! You're acting like little bitches! I'm not spending my whole day doing this while having to listen to you two moaning and whining the whole time. If you think this job is easy I invite you to try it yourself. If I could just be the bait myself, I would. But apprently our killer likes him some man booty, and you two gorgeous hunks are it. So pony the hell up."

They both grumbled but stopped fighting back and forth. You paid for breakfast and piled back into the Impala. You gave them directions to the place you thought would be most likely to have what you needed. You pulled up to a shop that was fully curtained behind a few mannequins in lingerie. The outside was bright pink and gold script informed passers by that the place was called Taboo Boudoir. The boys looked embarrassed and terrified at the same time.

"Out!" You commanded. They pulled themselves from the vehicle reluctantly and wouldn't be the first in the door. So you led them in, like shy little duckings. They couldn't help looking around once they were inside. The whole place smelled like strawberries, which you could see wasn't what they expected. Sam was actually moving towards the clothing. Dean, however, was distracted by the appliances.

"Hey, Y/N," Dean motioned you over, holding a box. He showed you the picture on the front and you choked a little. "What do you suppose this is for?" You snatched the box and set it back on the shelf.

"You don't want to know and that's not what we're here for."

You grabbed his elbow and practically dragged him over into the clothing section. Sam was looking at the size labels with a puzzled expression. As well he would be. Female sizes and male sizes were drastically different. You pulled the dress he had away from him and looked at the tag. It might be big enough. You held it up to him. 

"I don't think it's going to fit across the shoulders. Hmm..." You picked through some racks and found something that would lace. "Here, adjustable." 

Sam made a face that looked like he didn't believe it. You told him how he'd need to put it on and sent him off to the fitting room with a smack on the ass that he didn't appreciate. You turned to find Dean looking at something that belonged on Jessica Rabbit. You smothered your giggles at the thought of Dean in bright pink sequins. You were so so tempted to make him get it, but you took pity.

"Dean, please, no pink. It goes terribly with your coloring." He rolled his eyes at you and moved over to a rack that had a lot of black on it. You considered that for a moment. Dean didn't wear black. Like ever. Suddenly you wanted to see Dean in something black and racy. You joined him at the rack. You found a skirt in vinyl that was slit up both sides almost all the way to the waist. There was a top that matched almost exactly. Lots of silver zippers and black netting. Oh yes, that would work nicely.

"Go on, sweetie. Let's see it." You shoved him towards the rooms. Sam called you from one of the stalls and you followed his voice back.

"Problems, Sam?"

"I can't..." you heard rustling. "I can't get it tied. This is so fucking embarrassing. You never wear this shit! Why do we have to?"

"Firstly," you said as you entered the stall, seeing Sam trying to put the dress over his shirt. "Quit being such a prude. Take off your shirt. You can't wear the shirt with it tonight, so get used to it. You're also going to have to lose the boxers, but we'll ignore that for the moment, shy boy."

"As for why I don't wear this stuff, there's a couple of reasons." You straightened the dress and started pulling on laces. The soft peach color glowed against his golden skin. You wondered, as you usually did, how the hell he got so tanned sitting in the car all the time. He really was gorgeous. You fluffed the ruffles that just covered his ass. He met your eyes in the mirror and shifted uncomfortably.

"I don't wear it because I have no one to wear it for. Also, I'm not a whore to wear this stuff out in public. You, however, look amazing."

Sam practically blushed, cutting that little smile full of dimples at the floor. You pulled the dress off of him and left him to get dressed. This was definitely the one for him. Now to find shoes, which you hoped would be easier than the dresses. At that moment Dean opened the door to his dressing room. He was tugging at everything, trying to make it cover more. He looked like a cross beween Liza Minelli and a goth girls dream. Black was definitely a good color for him.

"Oh hell yeah. That's hot Dean." He glared at you, still trying to pull the skirt lower. With the slits in it it was a hopeless struggle, but still he tried. The dark color made every freckle on him glow against his pale skin. He was delicious. 

"Dean, stop pulling. You're going to rip it."

"It's so damn short! How the hell am I supposed to walk around like this?"

"You're going to get special undies and deal with it. Don't worry, honey, I'm not going to let you go out there unprepared. You'll be a professional by the time I'm done." You patted him on the cheek and sent him back in the room to get changed.

Sam had made his way back onto the floor and was looking at a wall of shoes. They came in all types, and some on display were clearly not for womens feet. It was one of the reasons you'd chosen the place. The peach outfit you'd chosen for Sam had white ribbons and bows discreetly accenting it. You took a look and found a pair of white platforms. They were high, but the platform should make it easier to walk in.

"Here, try these. Wait, what size are you?"

"Thirteen."

"That makes you a fifteen in womens..." you dug through the boxes and found them. "Here, these should fit."

Sam didn't look like he believed it, but he toed one of his boots off. You had to get him to take off his damned socks too because he seriously tried to shove his feet in the heels with his socks on! You asked if he planned to wear his socks with the dress and he sighed. The socks came off. He put one on and tried to stand. All six plus feet of him wobbled dangerously. You held up your hands, like you could stop that tree from falling.

"How the hell do you even walk in these?"

"It helps if you have both on." 

Sam glared, jaw clamped shut, and put the other one on. He stood, holding your hands like you were teaching him how to ice skate. He was struggling to keep his ankles straight. Laughter broke out from behind you.

"Oh my god! It's Cinderella's weird brother! How is it Princess?"

"You do realize that if I'm her weird brother then that makes YOU Cinderella."

"Don't mock him Dean. You're next." You could practically hear Dean swallow his laughter. It was like he didn't remember he'd agreed to high boots to avoid the shaving part. You helped Sam get down off the heels without falling over. Back in the box they went then Sam went and sat, his choices on the chair next to him.

Finding boots for Dean was harder than you'd thought. The problem with boots is that they didn't just have to fit in the foot, they had to fit in the calves too. That was an issue. You went through all the boots you could find and nothing would work. In the end you ended up commanding Dean to stay put while you went to ask the clerk. You know the boys couldn't hear the story you fed the guy behind the counter, but you knew they noticed his reaction. The man glanced over at both of them, tittered behind his hand, and went into the back of the store.

He came out with a very long box and handed it to you. You took it over to Dean and uncovered a fantastic set of boots. You were jealous as hell, actually. They were platform, heeled, combat boots. They were actual leather, and they laced with hooks all the way to the upper calf and had an open top over the knee, so you could cuff them down if you wanted. You made Dean lace them for himself. When he stood up he didn't wobble nearly as much as Sam had. He walked back and forth a few times and cocked his head..

"These aren't bad. Pretty comfortable and not nearly as hard to walk in as I thought."

"Yeah," Sam said from his chair. "That's because you practically have a full sized sole. If you had these thin heels you'd fall over as bad as I do."

"Good thing I don't, then." Dean smirked at his brother. "Me and my "bow legs" are going to be a hell of a lot more comfortable than you are Miss Priss. What do you think of that?"

"I'm still prettier." Sam shot back. 

You laughed. He was still right. Even the clerk laughed, having heard the interaction. You took everything up to the counter, including the "special underwear" you'd told the boys about. They were going to love those. You shook your head, smiling to yourself.

"You enjoy those boots, honey," the clerk winked at Dean. "I can always order more." Dean stiffened, pink rising in his cheeks. He walked out of the shop in shocked silence and climbed into the car.

"Dean? You ok?" Sam looked concerned.

"Never been hit on by a dude." He mumbled, like he was afraid to say it out loud.

"Oh, yeah. He was just being friendly. I told him about the size problem and he thought you were cute. So he went and got the ones he'd ordered for himself. You should thank your lucky stars he was willing to give them up. Those things are a work of art, and expensive as hell."

"I don't care how expensive they are. It's just weird to get hit on by a dude, that's all."

"Get used to it, cupcake." Sam smirked from the passenger seat. The boys were really enjoying each others discomfort entirely too much. That or they were bickering to destract themselves from this travesty of an outing. But you'd gotten the wardrobe out of the way.

"Hair next!"

A chorus of male groans and your laughter followed the sleek black Impala down the road to your next destination.


End file.
